Thienylpyrrole fungicidal agents

Abstract

There are provided fungicidal thienyl- and furylpyrrole compounds of formula I ##STR1## Further provided are compositions and methods comprising those compounds for the protection of plants from fungal infestation and disease.

What is claimed is: 
     
       1. A method for control or amelioration of a disease caused by a phytopathogenic fungus which comprises contacting said fungus with a fungicidally effective amount of a compound having the structural formula ##STR117## wherein R, R 1  and R 2  are each independently hydrogen, halogen, NO 2  or CHO, and when R 1  and R 2  are taken together with the carbon atoms to which they are attached, they may form a ring in which R 1  R 2  is represented by the structure: ##STR118## L, T, V and W are each independently hydrogen, halogen, CN or NO 2  ; A is S; X is CN, NO 2 , C 1  -C 6  haloalkyl, S(O) m  CF 2  R 3  or C(S)NR 4  R 5  ;   R 3  is hydrogen, F, Cl, Br, C CCl 3  ;   m is an integer of 0, 1 or 2;   R 4  and R 5  are each independently hydrogen, C 1  -C 4  alkyl optionally substituted with one or more halogen atoms, or   phenyl optionally substituted with one or more halogen atoms, NO 2  groups,   CN groups,   C 1  -C 4  alkyl groups optionally substituted with one or more halogen atoms, or   C 1  -C 4  alkoxy groups optionally substituted with one or more halogen atoms;       Y is hydrogen, halogen, C 1  -C 6  haloalkyl, S(O) m  CF 2  R 3 , CN or phenyl optionally substituted with one or more halogen atoms, NO 2  groups,   CN groups,   C 1  -C 4  alkyl groups optionally substituted with one or more halogen atoms, or   Cl-C 4  alkoxy groups optionally substituted with one or more halogen atoms;       Z is hydrogen, halogen or C 1  -C 6  haloalkyl;   B is R 6 , OR 6  or CN;   R 6  is hydrogen, C(O)R 7 , CHR 8  NHC(O)R 9 , CH 2  SQ, CHR 10  OC(O) (CR 11  R 12 ) n  Q 1 , C 1  -C 6  alkyl optionally substituted with one to three halogen atoms, one tri(C 1  -C 4  alkyl)silyl,   one hydroxy,   one cyano,   one or two C 1  -C 4  alkoxy groups optionally substituted with one to three halogen atoms,   one C 1  -C 4  alkylthio,   one phenyl optionally substituted with one to three halogen atoms, one to three C 1  -C 4  alkyl groups or one to three C 1  -C 4  alkoxy groups,   one phenoxy group optionally substituted with one to three halogen atoms, one to three C 1  -C 4  alkyl groups or one to three C 1  -C 4  alkoxy groups,   one benzyloxy group optionally substituted on the phenyl ring with one to three halogen atoms, one to three C 1  -C 4  alkyl groups or one to three C 1  -C 4  alkoxy groups,   one C 1  -C 6  alkylcarbonyloxy group optionally substituted with one to three halogen atoms,   one C 2  -C 6  alkenylcarbonyloxy group optionally substituted with one to three halogen atoms,   one phenylcarbonyloxy group optionally substituted with one to three halogen atoms, one to three C 1  -C 4  alkyl groups or one to three C 1  -C 4  alkoxy groups,   one C 1  -C 6  alkoxycarbonyl group optionally substituted with one to three halogen atoms or one to three C 1  -C 4  alkoxy groups, or   one benzylcarbonyloxy group optionally substituted on the phenyl ring with one to three halogen atoms, one to three C 1  -C 4  alkyl groups or one to three C 1  -C 4  alkoxy groups,     C 3  -C 6  alkenyl optionally substituted with one to three halogen atoms or one phenyl group, or   C 3  -C 6  alkynyl optionally substituted with one to three halogen atoms or one phenyl group;     R 7  is C 1  -C 6  alkyl or C 3  -C 6  cycloalkyl each optionally substituted with one to three halogen atoms, one hydroxy,   one cyano,   one or two C 1  -C 4  alkoxy groups optionally substituted with one to three halogen atoms,   one C 1  -C 4  alkylthio,   one phenyl group optionally substituted with one to three halogen atoms, one to three C 1  -C 4  alkyl groups or one to three C 1  -C 4  alkoxy groups,   one phenoxy group optionally substituted with one to three halogen atoms, one to three C 1  -C 4  alkyl groups or one to three C 1  -C 4  alkoxy groups,   one benzyloxy group optionally substituted on the phenyl ring with one to three halogen atoms, one to three C 1  -C 4  alkyl groups or one to three C 1  -C 4  alkoxy groups,   one C 1  -C 6  alkylcarbonyloxy group optionally substituted with one to three halogen atoms,   one C 2  -C 6  alkenylcarbonyloxy group optionally substituted with one to three halogen atoms,   one phenylcarbonyloxy group optionally substituted with one to three halogen atoms, one to three C 1  -C 4  alkyl groups or one to three C 1  -C 4  alkoxy groups,   one C 1  -C 6  alkoxycarbonyl group optionally substituted with one to three halogen atoms or one to three C 1  -C 4  alkoxy groups, or   one benzyloxycarbonyl group optionally substituted on the phenyl ring with one to three halogen atoms, one to three C 1  -C 4  alkyl groups or one to three C 1  -C 4  alkoxy groups,   C 2  -C 6  alkenyl optionally substituted with one to three halogen atoms or one phenyl groups,   C 3  -C 6  alkynyl optionally substituted with one to three halogen atoms or one phenyl group,   phenyl optionally substituted with one or more halogen atoms, C 1  -C 4  alkyl groups, C 1  -C 4  alkoxy groups, phenoxy groups, C 1  -C 4  alkylthio groups, tri(C 1  -C 4  alkyl)silyl groups, C 1  -C 4  alkylsulfinyl groups, C 1  -C 4  alkylsulfonyl groups, CN groups, NO 2  groups or CF 3  groups,   phenoxy optionally substituted with one or more halogen atoms, C 1  -C 4  alkyl groups, C 1  -C 4  alkoxy groups, C 1  -C 4  alkylthio groups, tri(C 1  -C 4  alkyl)silyl groups, C 1  -C 4  alkylsulfinyl groups, C 1  -C 4  alkylsulfonyl groups, CN groups, NO 2  groups or CF 3  groups,   1- or 2-naphthyl,   2-, 3-, or 4-pyridyl optionally substituted with one to three halogen atoms,   C 1  -C 6  alkoxy optionally substituted with one to three halogen atoms, or   C 2  -C 6  alkenyloxy optionally substituted with one to three halogen atoms;     R 8  is hydrogen or C 1  -C 4  alkyl;   R 9  is C 1  -C 6  alkyl optionally substituted with one to three halogen atoms, phenyl optionally substituted with one to three halogen atoms, CN groups, NO 2  groups, C 1  -C 4  alkyl groups, C 1  -C 4  alkoxy groups or CF 3  groups,   2- or 3-thienyl, or   2- or 3-furyl;     Q is ##STR119## CN, C 1  -C 6  alkyl optionally substituted with one or more halogen atoms, CN groups or phenyl groups, or phenyl optionally substituted with one or more halogen atoms, C 1  -C 4  alkyl groups, C 1  -C 4  alkoxy groups, CN groups, NO 2  groups, CF 3  groups or NR 24  R 25  groups;     A 1  is O or S;   R 13  is C 1  -C 6  alkyl or phenyl;   R 14  is C 1  -C 6  alkyl;   R 15  and R 16  are each independently hydrogen, C 1  -C 6  alkyl or may be taken together with the atom to which they are attached to form a 5- to 7-membered ring;   R 17  is C 1  -C 4  alkyl;   R 18  is hydrogen, C 1  -C 4  alkyl or may be taken together with either R 19  or R 21  and the atoms to which they are attached to form a 5- to 7-membered ring optionally substituted with one or two C 1  -C 4  alkyl groups;   R 19  and R 20  are each independently hydrogen or C 1  -C 4  alkyl;   R 21  is C 1  -C 4  alkyl or when taken together with R 18  and the atoms to which they are attached may form a 5- to 7-membered ring optionally substituted with one or two C 1  -C 4  alkyl groups;   R 22  and R 23  are each independently hydrogen or C 1  -C 4  alkyl or when taken together may form a ring wherein R 22  R 23  is represented by --CH═CH--CH═CH--;   R 24  and R 25  are each independently hydrogen or C 1  -C 4  alkyl;   R 10  is hydrogen or C 1  -C 4  alkyl;   R 11  and R 12  are each independently hydrogen, C 1  -C 6  alkyl optionally substituted with one or more halogen atoms,   C 1  -C 6  alkoxy optionally substituted with one or more halogen atoms,   C 1  -C 6  alkylthio optionally substituted with one or more halogen atoms, or   phenyl optionally substituted with one or more halogen atoms, NO 2  groups;   CN groups,   C 1  -C 4  alkyl groups optionally substituted with one or more halogen atoms, or   C 1  -C 4  alkoxy groups optionally substituted with one or more halogen atoms, or     when R 11  and R 12  are taken together with the atom to which they are attached may form a C 3  -C 6  cycloalkyl group optionally substituted with one to three C 1  -C 4  alkyl groups, C 2  -C 6  alkenyl groups or phenyl groups, or R 11  or R 12  may be taken together with R 26  and the atoms to which they are attached to form a 4- to 7-membered heterocyclic ring;     n is an integer of 0, 1, 2, 3 or 4;   Q 1  is A 2  R 26 , ##STR120## NR 28  R 29 , CR 30  R 31  C(O)R 32 , or C 3  -C 6  cycloalkyl optionally substituted with one or more C 1  -C 6  alkyl groups, C 2  -C 6  alkenyl groups, or   phenyl groups optionally substituted with one or more halogen atoms, NO 2  groups,   CN groups,   C 1  -C 4  alkyl groups optionally substituted with one or more halogen atoms, or   C 1  -C 4  alkoxy groups optionally substituted with one or more halogen atoms;       A 2  is O or S(O) p  ;   p is an integer of 0, 1 or 2;   R 26  is hydrogen, C 1  -C 6  alkyl   C 2  -C 6  alkenyl,   C 2  -C 6  alkynyl,   phenyl optionally substituted with one or more halogen atoms, NO 2  groups,   CN groups,   C 1  -C 4  alkyl groups optionally substituted with one or more halogen atoms,   C 1  -C 4  alkoxy groups optionally substituted with one or more halogen atoms,     C(O)R 33  provided p is O,   C(O)R 34  provided p is O,   (CH 2  CH 2  O) q  R 33 , or ##STR121## R 26  may be taken together with either R 11  or R 12  and the atoms to which they are attached to form a 4- to 7-membered heterocyclic ring;     A 3  is O or S;   R 33  is C 1  -C 6  alkyl, C 2  -C 6  alkenyl,   C 2  -C 6  alkynyl, or   phenyl optionally substituted with one or more halogen atoms, NO 2  groups,   CN groups,   C 1  -C 4  alkyl groups optionally substituted with one or more halogen atoms, or   C 1  -C 4  alkoxy groups optionally substituted with one or more halogen atoms;       q is an integer of 1, 2 or 3;   R 34  is OR 37  or NR 38  R 39  ;   R 37  is C 1  -C 6  alkyl or phenyl optionally substituted with one or more halogen atoms, NO 2  groups,   CN groups,   C 1  --C 4  alkyl groups optionally substituted with one or more halogen atoms, or   C 1  -C 4  alkoxy groups optionally substituted with one or more halogen atoms;     R 38  and R 39  are each independently hydrogen or C 1  -C 4  alkyl;   R 35  and R 36  are each independently hydrogen or C 1  -C 4  alkyl, or when taken together may form a ring wherein R 35  R 36  is represented by --CH═CH--CH═CH--;   R 27  is C 1  -C 4  alkyl;   R 28  is hydrogen, C 1  -C 6  alkyl,   C 2  -C 6  alkenyl,   C 2  -C 6  alkynyl, or   phenyl optionally substituted with one or more halogen atoms, NO 2  groups,   CN groups,   C 1  --C 4  alkyl groups optionally substituted with one or more halogen atoms, or   C 1  -C 4  alkoxy groups optionally substituted with one or more halogen atoms, or     R 28  may be taken together with either R 11  or R 12  and the atoms to which they are attached to form a 4- to 7-membered heterocyclic ring;     R 29  is hydrogen, C 1  -C 6  alkyl,   C 2  -C 6  alkenyl,   C 2  -C 6  alkynyl,   phenyl optionally substituted with one or more halogen atoms, NO 2  groups,   CN groups,   C 1  -C 4  alkyl groups optionally substituted with one or more halogen atoms, or   C 1  -C 4  alkoxy groups optionally substituted with one or more halogen atoms,     C(A 4 )R 40 ,   CN,   SO 2  R 41 , or   C(O)CHR 42  NHR 43  ;     A 4  is O or S;   R 40  is OR 44 , CO 2  R 44 , NR 45  R 46 , C 1  -C 6  alkyl optionally substituted with one to three halogen atoms,   C 2  -C 6  alkenyl,   C 2  -C 6  alkynyl, or   phenyl optionally substituted with one or more halogen atoms, NO 2  groups,   CN groups,   C 1  -C 4  alkyl groups optionally substituted with one or more halogen atoms, or   C 1  -C 4  alkoxy groups optionally substituted with one or more halogen atoms;       R 44  is C 1  -C 6  alkyl optionally substituted with one phenyl group, or phenyl optionally substituted with one or more halogen atoms, NO 2  groups,   CN groups,   C 1  -C 4  alkyl groups optionally substituted with one or more halogen atoms, or   C 1  -C 4  alkoxy groups optionally substituted with one or more halogen atoms;       R 45  and R 46  are each independently hydrogen or C 1  -C 4  alkyl;   R 41  is NR 47  R 48 , C 1  -C 6  alkyl,   C 2  -C 6  alkenyl,   C 2  -C 6  alkynyl, or   phenyl optionally substituted with one or more halogen atoms, NO 2  groups,   CN groups,   C 1  -C 4  alkyl groups optionally substituted with one or more halogen atoms, or   C 1  -C 4  alkoxy groups optionally substituted with one or more halogen atoms;       R 47  and R 48  are each independently hydrogen or C 1  -C 4  alkyl;   R 42  is hydrogen, C 1  -C 4  alkyl optionally substituted with one hydroxy group, one SR 49  group,   one C(O)NH 2  group,   one NH 2  group,   one NHC(═NH)NH 2  group,   one CO 2  H group,   one phenyl group optionally substituted with one hydroxy group,   one 3-indolyl group or   one 4-imidazolyl group;       R 49  is hydrogen or C 1  -C 4  alkyl;   R 43  is C(A 4 )R 50  ;   R 50  is C 1  -C 6  alkyl optionally substituted with one or more halogen atoms, C 1  -C 6  alkoxyalkyl,   C 1  -C 6  alkylthio,   phenyl optionally substituted with one or more halogen atoms, NO 2  groups,   CN groups,   C 1  -C 4  alkyl groups optionally substituted with one or more halogen atoms, or   C 1  -C 4  alkoxy groups optionally substituted with one or more halogen atoms,     OR 44 ,   CO 2  R 44  or   NR 45  R 46  ;     R 30  and R 31  are each independently hydrogen, C 1  -C 6  alkyl optionally substituted with one or more halogen atoms,   C 1  -C 6  alkoxy optionally substituted with one or more halogen atoms,   C 1  -C 6  alkylthio optionally substituted with one or more halogen atoms,   phenyl optionally substituted with one or more halogen atoms, CN groups,   NO 2  groups,   C 1  -C 4  alkyl groups optionally substituted with one or more halogen atoms, or   C 1  -C 4  alkoxy groups optionally substituted with one or more halogen atoms, or     when R 30  and R 31  are taken together with the atom to which they are attached may form a C 3  -C 6  cycloalkyl group optionally substituted with one to three C 1  -C 4  alkyl groups, C 2  -C 6  alkenyl groups or phenyl groups;     R 32  is OR 51 , NR 47  R 48 , C 1  -C 4  alkyl or phenyl optionally substituted with one or more halogen atoms, CN groups,   NO 2  groups,   C 1  -C 4  alkyl groups optionally substituted with one or more halogen atoms, or   C 1  -C 4  alkoxy groups optionally substituted with one or more halogen atoms; and     R 51  is C 1  -C 4  alkyl or phenyl optionally substituted with one or more halogen atoms, CN groups,   NO 2  groups,   C 1  -C 4  alkyl groups optionally substituted with one or more halogen atoms, or   C 1  -C 4  alkoxy groups optionally substituted with one or more halogen atoms; provided that when X is S(O) m  CF 2  R 3  and Z is hydrogen, then Y is hydrogen, halogen, C 1  -C 6  haloalkyl, S(O) m  CF 2  R 3  or CN; and further provided that when the pyrrole ring is substituted with hydrogen at each of the pyrrole carbon atoms adjacent to the ring nitrogen atom, then X cannot be CN or NO 2 .       
     
     
       2. The method according to claim 1 wherein R, R 1  and R 2  are each independently hydrogen, halogen or NO 2 , and when R 1  and R 2  are taken together with the carbon atoms to which they are attached, they may form a ring in which R 1  R 2  is represented by the structure: ##STR122## L, T, V and W are each independently hydrogen, halogen, CN or NO 2  ; A is S;   X is CN, NO 2 , C 1  -C 6  haloalkyl, S(O) m  CF 2  R 3  or C(S)NR 4  R 5  ;   R 3  is hydrogen, F, Cl, Br, CF 2  H, CCl 2  H, CClFH, CF 3  or CCl 3  ;   m is an integer of 0, 1 or 2;   R 4  and R 5  are each independently hydrogen, C 1  -C 4  alkyl optionally substituted with one or more halogen atoms or   phenyl optionally substituted with one or more halogen atoms, NO 2  groups,   CN groups,   C 1  -C 4  alkyl groups optionally substituted with one or more halogen atoms, or   C 1  -C 4  alkoxy groups optionally substituted with one or more halogen atoms;       Y is hydrogen, halogen, C 1  -C 6  haloalkyl, S(O) m  CF 2  R 3 , CN or phenyl optionally substituted with one or more halogen atoms, NO 2  groups,   CN groups,   C 1  -C 4  alkyl groups optionally substituted with one or more halogen atoms, or   C 1  -C 4  alkoxy groups optionally substituted with one or more halogen atoms;       Z is hydrogen, halogen or C 1  -C 6  haloalkyl;   B is R 6  or CN;   R 6  is hydrogen, C(O) 7  or C 1  -C 6  alkyl optionally substituted with one to three halogen atoms, one cyano,   one C 1  -C 4  alkoxy group,   one C 1  -C 6  alkylcarbonyloxy group,   one phenylcarbonyloxy group, or   one benzylcarbonyloxy groups; and       R 7  is phenyl optionally substituted with one or more halogen atoms, C 1  -C 4  alkyl groups, C 1  -C 4  alkoxy groups, CN groups, NO 2  groups or CF 3  groups.   
     
     
       3. The method according to claim 2 wherein R, R 1  and R 2  are each independently hydrogen, halogen or NO 2 , and when R 1  and R 2  are taken together with the carbon atoms to which they are attached, they may form a ring in which R 1  R 2  is represented by the structure: ##STR123## L, T, V and W are each independently hydrogen, halogen, CN or NO 2  ; A is or S;   X is CN, NO 2  or C 1  -C 6  haloalkyl;   Y is hydrogen, halogen, C 1  -C 6  haloalkyl or phenyl optionally substituted with one or more halogen atoms, NO 2  groups,   CN groups,   C 1  -C 4  alkyl groups optionally substituted with one or more halogen atoms, or   C 1  -C 4  alkoxy groups optionally substituted with one or more halogen atoms;     Z is hydrogen, halogen or C 1  -C 6  haloalkyl;   B is R 6  or CN;   R 6  is hydrogen, C(O)R 7  or C 1  -C 6  alkyl optionally substituted with one to three halogen atoms, one cyano,   one C 1  -C 4  alkoxy group,   one C 1  -C 6  alkylcarbonyloxy group,   one phenylcarbonyloxy group, or   one benzylcarbonyloxy group; and     R 7  is phenyl optionally substituted with one or more halogen atoms, C 1  -C 4  alkyl groups, C 1  -C 4  alkoxy groups, CN groups, NO 2  groups or CF 3  groups.   
     
     
       4. The method according to claim 3 wherein R, R 1  and R 2  are each independently hydrogen, halogen or NO 2 , and when R 1  and R 2  are taken together with the carbon atoms to which they are attached, they may form a ring in which R 1  R 2  is represented by the structure: ##STR124## L, T, V and W are each independently hydrogen, halogen, CN or NO 2  ;   A is S;   X is CN, NO 2  or C 1  -C 6  haloalkyl;   Y is hydrogen, halogen, C 1  -C 6  haloalkyl or phenyl optionally substituted with one or more halogen atoms, NO 2  groups,   CN groups,   C 1  -C 4  alkyl groups optionally substituted with one or more halogen atoms, or   C 1  -C 4  alkoxy groups optionally substituted with one or more halogen atoms;     Z is halogen or C 1  -C 6  haloalkyl;   B is R 6  or CN;   R 6  is hydrogen, C(O)R 7  or C 1  -C 6  alkyl optionally substituted with one to three halogen atoms, one cyano,   one C 1  -C 4  alkoxy group,   one C 1  -C 6  alkylcarbonyloxy group,   one phenylcarbonyloxy group, or   one benzylcarbonyloxy group; and     R 7  is phenyl optionally substituted with one or more halogen atoms, C 1  -C 4  alkyl groups, C 1  -C 4  alkoxy groups, CN groups, NO 2  groups or CF 3  groups.   
     
     
       5. The method according to claim 3 wherein R, R 1  and R 2  are each independently hydrogen, halogen or NO 2 , and when R 1  and R 2  are taken together with the carbon atoms to which they are attached, they may form a ring in which R 1  R 2  is represented by the structure:   --CH═CH--CH═CH--;       A is S;   X is CN or NO 2  ;   Y is halogen, CF 3  or phenyl optionally substituted with one or more halogen atoms, NO 2  groups,   CN groups,   C 1  -C 4  alkyl groups optionally substituted with one or more halogen atoms, or   C 1  -C 4  alkoxy groups optionally substituted with one or more halogen atoms;     Z is hydrogen, halogen or CF 3  ; and   B is hydrogen or C 1  -C 6  alkyl substituted with one C 1  -C 4  alkoxy group.   
     
     
       6. The method according to claim 5 wherein R, R 1  and R 2  are each independently hydrogen, halogen or NO 2  ;   A is S;   X is CN or NO 2  ;   Y is halogen, CF 3  or phenyl optionally substituted with one or more halogen atoms, NO 2  groups,   CN Groups,   C 1  -C 4  alkyl groups optionally substituted with one or more halogen atoms, or   C 1  -C 4  alkoxy groups optionally substituted with one or more halogen atoms;     Z is CF 3  ; and   B is hydrogen or C 1  -C 6  alkyl substituted with one C 1  -C 4  alkoxy group.   
     
     
       7. The method according to claim 5 wherein the compound is selected from the group consisting of 2-(2-thienyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile;   4-bromo-2-(5-bromo-2-thienyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile;   3-(5-bromo-3-thienyl)-5-(p-chlorophenyl)-4-nitro-2-(trifluoromethyl)pyrrole   2-chloro-5-(5-chloro-2-thienyl)pyrrole-3-carbonitrile; and   2-(p-chlorophenyl)-3-nitro-4-(5-nitro-2-thienyl)-5-(trifluoromethyl)pyrrole.   
     
     
       8. The method according to claim 1 wherein the compound is applied at a concentration of about 20 ppm to 1,000 ppm. 
     
     
       9. A method for the protection of a plant, plant seed or tuber from fungal infestation and disease which comprises applying to the plant, plant seed or tuber, or to the medium or water in which it is growing, a fungicidally effective amount of a compound having the structural formula ##STR125## wherein R, R 1 , R 2 , A, X, Y, Z and B are as described in claim 1. 
     
     
       10. The method according to claim 9 wherein R, R 1 , R 2 , A, X, Y, Z and B are as described in claim 2. 
     
     
       11. The method according to claim 10 wherein R, R 1 , R 2 , A, X, Y, Z and B are as described in claim 3. 
     
     
       12. The method according to claim 11 wherein R, R 1 , R 2 , A, X, Y, Z and B are as described in claim 4. 
     
     
       13. The method according to claim 11 wherein R, R 1  and R 2  are each independently hydrogen, halogen or NO 2 , and when R 1  and R 2  are taken together with the carbon atoms to which they are attached, they may form a ring in which R 1  R 2  is represented by the structure:   --CH═CH--CH═CH--;     A is S;   X is CN or NO 2  ;   Y is halogen, CF 3  or phenyl optionally substituted with one or more halogen atoms, NO 2  groups,   CN groups,   C 1  -C 4  alkyl groups optionally substituted with one or more halogen atoms, or   C 1  -C 4  alkoxy groups optionally substituted with one or more halogen atoms;     Z is hydrogen, halogen or CF 3  ; and   B is hydrogen or C 1  -C 6  alkyl substituted with one C 1  -C 4  alkoxy group.   
     
     
       14. The method according to claim 13 wherein R, R 1  and R 2  are each independently hydrogen, halogen or NO 2  ; A is S;   X is CN or NO 2  ;   Y is halogen, CF 3  or phenyl optionally substituted with one or more halogen atoms, NO 2  groups,   CN groups,   C 1  -C 4  alkyl groups optionally substituted with one or more halogen atoms, or   C 1  -C 4  alkoxy groups optionally substituted with one or more halogen atoms;     Z is CF 3  ; and   B is hydrogen or C 1  -C 6  alkyl substituted wtih one C 1  -C 4  alkoxy group.   
     
     
       15. The method according to claim 13 wherein the compound is selected from the group consisting of 2-(2-thienyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile;   4-bromo-2-(5-bromo-2-thienyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile;   3-(5-bromo-3-thienyl)-5-(p-chlorophenyl)-4-nitro-2-(trifluoromethyl)pyrrole;   2-chloro-5-(5-chloro-2-thienyl)pyrrole-3-carbonitrile; and   2-(p-chlorophenyl)-3-nitro-4-(5-nitro-2-thienyl)-5-(trifluoromethyl)pyrrole.   
     
     
       16. A composition for controlling phytopathogenic fungi which comprises an inert liquid or solid carrier and a fungicidally effective amount of a compound having the structural formula ##STR126## wherein R, R 1 , R 2 , A, X, Y, Z and B are as described in claim 1. 
     
     
       17. The composition according to claim 16 wherein R, R 1 , R 2 , A, X, Y, Z and B are as described in claim 2. 
     
     
       18. The composition according to claim 17 wherein R, R 1 , R 2 , A, X, Y, Z and B are as described in claim 3. 
     
     
       19. The composition according to claim 18 wherein R, R 1 , R 2 , A, X, Y, Z and B are as described in claim 4. 
     
     
       20. The composition according to claim 18 wherein R, R 1  and R 2  are each independently hydrogen, halogen or NO 2 , and when R 1  and R 2  are taken together with the carbon atoms to which they are attached, they may form a ring in which R 1  R 2  is represented by the structure: --CH═CH--CH═CH--;   A is S;   X is CN or NO 2  ;   Y is halogen, CF 3  or phenyl optionally substituted with one or more halogen atoms, NO 2  groups,   CN groups,   C 1  -C 4  alkyl groups optionally substituted with one or more halogen atoms, or   C 1  -C 4  alkoxy groups optionally substituted with one or more halogen atoms;     Z is hydrogen, halogen or CF 3  ; and   B is hydrogen or C 1  -C 6  alkyl substituted with one C 1  -C 4  alkoxy group.